Riches to Rags: When Sports Stars Go Broke

Joel Anderson |

athletes with money trouble, athletes who are broke, athletes who went to jailIt's easy to forget, amidst the on-field glory of a brilliant athletic career, that success in the sporting arena doesn't always translate into success off of it. For every Magic Johnson or Roger Staubach, there's a number of athletes who simply could not keep their lives together when they weren't on the field of play. For everything these athletes accomplished in their careers, they seemed equally capable of humanizing themselves before the whole world through serious errors in judgment.

Lenny Dykstra

Lenny Dykstra is prominently featured in Michael Lewis' seminal book Moneyball, but he did not make it into the last year's Oscar-nominated film adapted from the book. The picture painted of Dykstra in the book, as a visceral player who thought little and played with his gut, was especially important to understanding how Billy Beane would ultimately learn to see past traditional approaches to baseball scouting when identifying talent.

However, Lenny Dykstra's success after his career, at least for a while, made it appear as though the picture of Dykstra as a person who rarely thought things out started to lose credibility. In 2008, Dykstra started a chartered jet company that was intended to help him sell his financial advice to professional athletes through his company Nail Investment (Dykstra's nickname in his playing days was ("Nails"). However, by early 2009 it began to become clear that Dykstra's financial empire was more like Billy Beane's swing than his own. An investigation from revealed over a dozen legal actions taken against Dykstra since 2007 and Nails ultimately had to file for chapter 11 bankruptcy in July of 2009. While his net worth had been listed as high as $58 million in 2008, the bankruptcy filing revealed only $50,000 in assets against over $30 million is liabilities. Dykstra ultimately had to sell off his 1986 World Series ring he won with the Mets and then, in 2011, landed in legal trouble after it was revealed that he had hidden or destroyed assets to avoid listing them in his bankruptcy.

Denny McClain

Denny McLain is almost certain to go down as the last starting pitcher in baseball history to win 30 or more games in a season. In 1968, McLain won 31 games while en route to a World Series victory with the Detroit Tigers and winning the MVP as a starting pitcher, also a rare feat. However, McLain's career would fizzle out in the years to come, making 1968 the high water mark for McLain's career.

However, life after baseball proved problematic for McLain. McLain had a gambling problem, which resulted in an injured foot during the 1967 season reportedly coming from a bookie stomping on it for unpaid debts and McLain was ultimately suspended for three months in the 1970 season due to his gambling. McLain would ultimately purchase the Peet Packing Company in Chesaning, MI in 1994 only to see the company go bankrupt two years later. McLain was ultimately convicted on charges of embezzlement, mail fraud, and conspiracy involving the theft of $2.5 million from the Farmer Peet's pension fund. McLain, who also saw jail time for drug trafficking and racketeering, would ultimately have to take a job at a 7-1 1 in Sterling Heights, MI as a part of his work release program where he would sign autographs for Tigers fans.

Terrell Owens

Terrell Owens' troubles with finding a football team that he couldn't sabotage through his megalomania and toxic personality were well documented, but they also speak to just how much of a game-changer he could be at wide receiver. The fact that any team would want him after his public flap with Donovan McNabb led to the unraveling of a Super Bowl caliber Eagles team is proof that, despite being damaged goods, Owens kept convincing teams he was worth rolling the dice on.

Now, though, Owens no longer has the explosive talents he once did. He also hasn't retired despite having lost his edge, signing a contract for six-figures to play in the Indoor Football League's Allen Wranglers. Does T.O. love the game so much that he just can't let go? Has he swallowed his pride just to keep playing football even if he can't cut it in the NFL anymore? Possibly not. The Atlanta mother of one of TO's children claims that he's $20,000 past due on paying her child support, having failed to pay since December of last year. The receiver also claimed on his VH1 reality show, The T.O. Show, to be tapped out of funds despite making tens of millions of dollars over the course of his playing career. Owens is also in foreclosure for two of his Dallas-area homes. While it's still unclear whether or not Terrell Owens is really broke, his issues with nonpayment of child support could end up with the wide receiver landing in jail.

DISCLOSURE: The views and opinions expressed in this article are those of the authors, and do not represent the views of Readers should not consider statements made by the author as formal recommendations and should consult their financial advisor before making any investment decisions. To read our full disclosure, please go to:


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